269. Anomalous resistance to oxidation of hydroxyl groups in some bicyclo[2,2,1]heptane derivatives

Crundwell, E.; Templeton, William K.

doi:10.1039/jr9640001400

Cited by 18 publications

(3 citation statements)

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“…22,23 Norbornane lactone acrylate 11 (NLA) (Figure 1) was synthesized according to the literature. 24,25 Commercially available dimethyl-2,2'-azobisisobutylate (V-601) was used as the initiator for free radical polymerization. Triphenylsulfonium triflate (TPSOTf) (Midori Kagaku Co.) was used as a photo-acid generator.…”

Section: Methodsmentioning

confidence: 99%

Development of high-performance negative-tone resists for 193-nm lithography

Hattori

Yokoyama

Kimura

et al. 2003

Advances in Resist Technology and Processing XX

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We have been developing negative-tone resist systems utilizing an acid-catalyzed intramolecular esterification of γ-and δ-hydroxy acid for ArF phase-shifting lithography. In this paper, α−acryloyloxy-β,β-dimethyl-γ-butyrolactone (DBLA), adamantane lactone acrylate (AdLA), and norbornane lactone acrylate (NLA) were examined as a precursor of hydroxy acid. It was found that AdLA and NLA are not hydrolyzed into hydroxy acid under an alkali hydrolysis condition. DBLA was found to produce γ-hydroxy acid, which is stable in the resist solution. The γ-hydroxy acid derived from DBLA becomes γ-lactone relatively easily by an acid-catalyzed reaction and can be used to make resists insoluble.Since the variation and the flexibility of the copolymer composition of the base polymer can be increased, the resist properties are controllable and the pattern quality can be improved by utilizing γ-hydroxy acid derived from DBLA.

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Section: Methodsmentioning

confidence: 99%

Development of high-performance negative-tone resists for 193-nm lithography

Hattori

Yokoyama

Kimura

et al. 2003

Advances in Resist Technology and Processing XX

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“…Discussion. The halolactones obtained flora the broruination (Roberts, Trumbull, Bennett & Armstrong, 1950) or iodination (Ver Nooy & Rondestvedt, 1955) of 5-norbornene-2-endo-carboxylic acid have assumed a central role in the spectral and structural correlations of many norbornyl derivatives (Crundwell & Templeton, 1964;Ramey, Lini, Moriarty, Gopal & Welsh, 1967;Ford, Kitching & Wells, 1969;Beck.mann & Geiger, 1961;Beckmann, Eder & Geiger, 1969). Initially the 2,6-bridged structure was assumed for these compounds, without any apparent justification.…”

Section: Introductionmentioning

confidence: 99%

“…The halolactones obtained flora the broruination (Roberts, Trumbull, Bennett & Armstrong, 1950) (Crundwell & Templeton, 1964;Ramey, Lini, Moriarty, Gopal & Welsh, 1967;Ford, Kitching & Wells, 1969;Beck.mann & Geiger, 1961;Beckmann, Eder & Geiger, 1969).…”

Section: Introductionmentioning

confidence: 99%

5-exo-Bromo- and 5-exo-iodo-6-endo-norbornanol-2-endo-carboxylic acid lactones

Singh¹,

Hodgson²

1974

Acta Crystallogr Sect B

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Abstract. CsH9OzBr, monoclinic, P2~/c, a=6-383 (4), b=ll.180 (6), c=11.430 (7)A, /~=95.76 (3) °, Z=4, D~= 1-78, D,,= 1.76 (2) g cm -3. C8H902I, orthorhombic, Pbca, a=11.825 (6), b=15-609 (25), c= 11.310 (7)/~, Z= 16, D¢=2.05, D,,,=2.11 (5) g cm -3. The bromolactone, and both independent molecules of the iodolactone, exist in the 2,6-bridged configuration with normal bond lengths. The bond angles, however, show considerable departure from their ideal values. The angle at the bridging carbon atom is 94.8 (4) ° for the bromolactone and 103 (2) and 101 (2) ° for the two molecules of iodolactone.Introduction.

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Die Synthese von 6‐substituierten 2‐Norbornanolen. Norbornane, 7. Mitteilung

Grob

Günther

Waldner

1981

Helvetica Chimica Acta

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The preparation of several 6-exo-and 6-endo-substituted 2-exo-and 2-endonorbornanols and their p-toluenesulfonates is described.Fur eine mechanistische Untersuchung, uber die kurzlich berichtet worden ist [ lI3), wurden die p-Toluolsulfonsaureester l a -l i der entsprechenden 6-endo-substituierten 2-exo-Norbornanole 2 a-2 i benotigt4). Im folgenden wird die Synthese dieser Verbindungen beschrieben, einschliesslich die Herstellung einiger zum Vergleich benotigter 6-exo-alkylsubstituierter 2-exo-und 2-endo-Norbornanole 4 bzw. 6 sowie ihrer p-Toluolsulfonsaureester 3 und 5 .Als Ausgangsmaterial fur die meisten der zum grossten Teil noch unbekannten 6-endo-substituierten Verbindungen 1 und Z5) diente der 6-exo-Hydroxy-2-endonorbornancarbonsauremethylester (2b), welcher durch Hydroborierung des bekannten 5-Norbornen-2-endo-carbonsauremethylesters (7) [7] in einem (3 : 2)-Gemisch mit dem 5-exo-Hydroxyester 8b erhalten wurde. Eine Auftrennung gelang durch fraktionierte Kristallisation der entsprechenden Carbonsauren 2 a und 8 a. Behandlung des reinen Methylesters 2 b mit p-Toluolsulfonylchlorid (Tosylchlorid) in Pyridin nach 24 Std. bei 22" fuhrte zump-Toluolsulfonsaureester lb. Die Struktur von 2 a und 2 b wurde mittels der 13C-NMR.-Spektren sichergestellt, wobei die gefundenen Daten im Falle der 2,6-1someren 2 jeweils gut mit den berechneten ubereinstimmten. Die C, H-Kopplungen in den ctoff-re~onance)>-'~C-NMR.-Spektren waren zudem mit den Strukturen 2 a und 2 b im Einklang (vgl. Tub.). I ) 2,Korrespondenzautor. 3, 4, s,Der neue IUPAC-Name von ((Norbornan)) ist 8,9,10-Trinorbornan, Vgl. auch die vorlaufigen Mitteilungen [2]. Uber die Herstellung entsprechender 6-exo-substituierter 2-exo-und 2-endo-Norbornanole 4 bzw. 6 und ihrerp-Toluolsulfonsaureester 3 bzw. 5 ist bereits berichtet worden [3]. Bekannt sind nur der Methylester 2h [4] sowie das Methyl-[5] und Brommethyl-Derivat [6] 2h bzw. 2i.

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269. Anomalous resistance to oxidation of hydroxyl groups in some bicyclo[2,2,1]heptane derivatives

Cited by 18 publications

References 0 publications

Development of high-performance negative-tone resists for 193-nm lithography

Development of high-performance negative-tone resists for 193-nm lithography

5-exo-Bromo- and 5-exo-iodo-6-endo-norbornanol-2-endo-carboxylic acid lactones

Die Synthese von 6‐substituierten 2‐Norbornanolen. Norbornane, 7. Mitteilung

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